Trisazo dyestuffs



Patented Oct. 8, 1929 1 UNITED STATES PATENT OFFICE HUGO SCHWEITZER ANDJOHANN HUISMANN, OF WIESDORF-ON-THE-RHINE, GER

MANY, ASSIGNORS TO GENERAL ANILINE WORKS, INQ, NEW YORK, N. Y., A

CORPORATION OF DELAWARE TBISAZO DYESTUFFS No Drawing. Application filedApril 26, 1927, Serial No. 186,814, and in Germany May 17, 1926.

The present inventionrelates to azo dyestuffs of the general formulaOCzHs radicle of a l-amino-2-naphthol ether with a 2 amino 5naphthol-7-sulfonic acid compound.

The new dyestuffs are generally dark powders soluble in water with abluish-green and in concentrated sulfuric acid with a blue coloration,dyeing cotton in clear greenish blue shades of good fastness propertiesand yield ing by reduction with stannous chloride and hydrochloric acid,sulfonic acids of aromatic amines, aromatic diamines and their sulfonicacids; 2 ethoxy, 14 naphthylene diamine The naphthylamine 7-sulfonicacid in about 500 c. c. of water. When the coupling is complete, 60 c.c. of commercial hydrochloric acid are run into the mixture anddiazotation is effected with 69 c. c. of a 10% sodium nitritesuspendedin 300 c. c. of water; ice is caused to float in thesuspension, and 8 c. c. of caustic soda solution (30 B.) are added'withbrisk stirring. 7 0 c. c. of a 10% sodium nitritesolution are nowintroduced and the dyestuif is dia-zotized by causing 60 c. c. ofcommercial hydrochloric acid to run in. The resulting diazo solution isthen added to an ice cold solution of 31.5 grams ofQ-phenylamino-5-naphthol-7-sulfonic acid in cc. of water'and 100 c. c.of pyridine. When the coupling is complete the dyestuff is worked up inthe known manner." The dyestuff has most probably the formula OC2H5SOaNa f dOiNa This dyestuff represents indry statea blu ish-black powdersoluble in waterwith a greenish-blue and in concentrated sulfuric acidwith a pure blue coloration. It dyes cotton in a clear greenish blueshade of good fast= ness properties especially fastness to light. Thedyestufl' yields by reduction with stannous chloride and hydrochloricacid aniline- 3.6-disulfonic acid B031 1 V I 45 RN=N-N=N A N=N s oma nno 7 O Y x V I i H v a r c 1,4 naphthylene-dia1nine-7-sultonic acidconcentrated sulfuric acid With a pure lolue coloration and which dyescotton clear bluish- N111 green shades of good fastness to light.

' In testimony whereof e have hereunto set 5 7 our hands. I I a J 70HUGO SCHVVEITZER.

JOHANN HUISMANN. 2-eth0xy-IA-naphthylened1a1n1ne Q'C2 s r 10 75 H2N NH2v V and 2-pheny1amino-6-5-=mino nziphthol-7- sulfonic acid r so H03s-'NH-O HzN OH 7 v 85 In analogous manner further dyestuffs can be producedby replacing the Q-phenylzunine-5-naphthol-7 sulfonic acid by 2-a1n-ino5-naphthol-7-sulfonic acid or its derivatives 9 and substitutionproducts.

We cl'aiinz I. As new products the trisazo dyestuffs of the generalformula: .0 i V OCZH5 r V V ,5

R--'N'=NYR1N=N N=;N Qa fl wherein R and R represent aryl'nu'clei and a40 Y represents hydrogen or an aryl nucleus. i v v j. i r V v 7 2.v-As-new products .thetrisazo dyestuffs of the general formula: I Oc i asome -NH.Y 11

wherein R represents an aryl nucleus and Y represents hydrogeno'r anaryl nucleus.

3. As a newproduct the azo dyestufi' of the probable formula soaNa v 002115 some 7 his Ne l M some 1 s oam' H i Which in a dry'st'at e is ablue-black powder 65 soluble inwater Wltll'fi, greenish-blue and inCertificate of Correction Patent No. 1,730,692. Granted October 8 1929,to

HUGO SGHWEITZER ET AL.

It is hereby certified that error appears in the printed specificationof the above numbered patent requiring correction as follows: Page 1,line 28, for 14 read 1, 4; same page strike out the second formuia andthe corresponding formula of claim 3 on page 2 and insert instead OaNaand that the said Letters Patent should be read with these correctionstherein that the same may conform to the record of the case in thePatent Office.

Signed and sealed this 18th day of February, A. D. 1930.

[sEAn] M. J. MOORE,

Acting Commissioner of Patents, I v

